Top 10% of guest reviews in this areaTop 10% of guest reviews in this area
Highlights
The great outdoors
Guests love the outdoor space here.
Outdoor pool
The outdoor pool is a refreshing retreat under the open sky - a rare gem in this area.
Centrally-located
You're never far from where you need to be with this convenient location.
4 bedrooms3 bathroomsSleeps 10
Popular amenities
Private pool
Onsite parking available
Kitchen
Washing machine
Air-conditioning
Barbecue
Explore the area
Cambridge, MD
Christ Rock Park
Place, Christ Rock Park
6 min drive
Harriet Tubman Museum and Educational Center
Place, Harriet Tubman Museum and Educational Center
11 min drive
Long Wharf Park
Place, Long Wharf Park
12 min drive
Easton, MD (ESN-Easton - Newnam)
Airport, Easton, MD (ESN-Easton - Newnam)
48 min drive
Where you'll sleep
4 bedrooms (sleeps 10)
B&O Railroad Room
1 Queen Bed
Captain's Quarters
1 King Bed
Chesapeake Room
1 King Bed and 2 Single Beds
Pineapple Room
1 Queen Bed
3 bathrooms
Captains Bath
Towels provided · Toilet · Shower only
lower level bath
Towels provided · Toilet · Shower only · Hair dryer
Pineapple Bath
Towels provided · Bathtub or shower · Toilet
Spaces
Deck or patio
Porch or lanai
Kitchen
Separate dining area
Outdoor play area
About this property
Family-Friendly Waterfront Retreat w/ Pool, Dock, Firepit & Game Room
Waterfront Retreat on 4 Private Acres | Pool, Dock, Kayaks & Game Barn
Welcome to your private Eastern Shore escape—where peaceful waterfront views, wide-open space, and thoughtful luxury come together for an unforgettable stay.
For nearly a decade, we’ve welcomed guests to this special property, and once you arrive, you’ll understand why so many return year after year. As you wind down the quarter-mile driveway past a 200+ year-old sycamore, the stress of everyday life begins to fade. When the red barn and swaying willow trees come into view—you’ve arrived.
The Home
Step inside our beautifully restored stone house and take in sweeping views of Fishing Creek through a stunning wall of floor-to-ceiling windows.
The open-concept great room is designed for connection and comfort, featuring:
A fully equipped modern kitchen Oversized dining table + custom island seating Plush seating for your entire group Easy access to the screened-in porch—perfect for sunset breezes Sleeping Arrangements (Sleeps Large Groups Comfortably)
Main Level:
B&O Railroad Room: Queen bed Chesapeake Room: King bed + twin trundle (2 beds) Full bathroom
Upper Level (2 Private Suites):
Captain’s Quarters: King bed, ensuite bath, walk-in closet Pineapple Room: Queen bed, ensuite bath, walk-in closet Each suite includes a rollaway twin for added flexibility
Perfect for families, multi-generational groups, or friends traveling together.
Outdoor Living & Waterfront Fun
This is where the property truly shines:
Private dock for crabbing, fishing, or relaxing by the water Kayaks & paddleboards available for guest use Gentle boat ramp for your own watercraft 4 scenic acres to explore, play, and unwind Pool + Barn Saltwater pool with tanning ledge + umbrella seating Expansive barn game room with: Pool table Ping pong Air hockey Darts
Plus a large open field for cornhole, croquet, or your favorite outdoor games.
Evenings to Remember Gas grill for easy cookouts Fire pit with provided firewood Perfect setting for s’mores, stargazing, and storytelling Explore the Area
Located near charming Cambridge, you’re close to some of the Eastern Shore’s best experiences:
Waterfront dining with fresh local seafood Breweries and shops along Race Street Nature and wildlife at Blackwater National Wildlife Refuge History at the Harriet Tubman Underground Railroad Visitor Center Resort amenities and golf at Hyatt Regency Chesapeake Bay Golf Resort, Spa and Marina Your Stay
You’ll have full, private access to the property during your stay. Occasionally, we may be in the barn loft apartment when not traveling—but we fully respect your privacy. If you’d like local tips or a friendly chat, we’re always happy to connect.
Why Guests Love It
✔ Waterfront + private dock ✔ Pool + game barn = fun for all ages ✔ Peaceful, secluded setting (yet close to town) ✔ Ideal for families & group getaways ✔ Thoughtfully designed for relaxation and connection
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Absolutely no jumping or diving into the swimming pool or creek. No running on the pool deck or dock. No glass containers in the swimming pool area.
Life preservers must be worn by anyone under age 16 while on watercraft. All others must have life preservers with them while on watercraft.
Please be respectful of our neighbors, especially at night. Noise carries along waterways.
Important information
You need to know
Property # 954012vb
Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
On-site parties or group events are strictly prohibited
Host has indicated that there is a carbon monoxide detector on the property
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher, a first aid kit and a deadlock
This property has outdoor spaces, such as balconies, patios and terraces, which may not be suitable for children; if you have any concerns, we recommend contacting the property prior to your arrival to confirm that they can accommodate you in a suitable room
About the area
Cambridge
Located in Cambridge, this holiday home is in a rural area and on the waterfront. The area's natural beauty can be seen at Chesapeake Bay and Blackwater National Wildlife Refuge, while Harriet Tubman Museum and Educational Center and Richardson Maritime Museum are cultural highlights. Travelling with kids? Consider Dorchester Arts Center and Ruark Boatworks. Discover the area's water adventures with kayaking and power boating nearby, or enjoy the great outdoors with cycling and hiking/biking trails.
Harriet Tubman Museum and Educational Center - 11 min drive - 10.3 km
Long Wharf Park - 12 min drive - 11.0 km
Choptank River Lighthouse - 12 min drive - 11.0 km
Getting around
Cambridge Station - 14 min drive
Easton, MD (ESN-Easton - Newnam) - 36 min drive
Restaurants
McDonald's - 11 min drive
Chick-fil-A - 11 min drive
Dunkin' - 11 min drive
Thaitalian Infusion Cuisine - 9 min drive
Great Wall #2 - 10 min drive
Frequently asked questions
Does Family-Friendly Waterfront Retreat w/ Pool, Dock, Firepit & Game Room have a pool?
Yes, this property has an outdoor pool.
Is Family-Friendly Waterfront Retreat w/ Pool, Dock, Firepit & Game Room pet-friendly?
No, pets are not allowed at this property.
How much is parking at Family-Friendly Waterfront Retreat w/ Pool, Dock, Firepit & Game Room?
On-site parking is available at the property.
What time is check-in at Family-Friendly Waterfront Retreat w/ Pool, Dock, Firepit & Game Room?
Check-in begins at 4:00 PM.
What time is check-out at Family-Friendly Waterfront Retreat w/ Pool, Dock, Firepit & Game Room?
Checkout is at 11:00 AM.
Where is Family-Friendly Waterfront Retreat w/ Pool, Dock, Firepit & Game Room located?
This family-friendly Cambridge holiday home is located on the waterfront, within 3 mi (5 km) of Christ Rock Park and Snows Turn Park. Richardson Maritime Museum and Dorchester Arts Center are also within 6 miles (10 km).
About the host
Hosted by Rob and Gretchen Dejter
Welcome to Sailor’s Retreat—your peaceful escape on Maryland’s beautiful Eastern Shore.
As we enter our ninth summer of hosting, we feel incredibly grateful to share this special property with guests. Our goal is simple: to offer a relaxing, comfortable, and memorable stay in a setting that feels both private and welcoming.
The name Sailor’s Retreat reflects our love of sailing the local waterways and everything that makes this area so special. We hope you’ll enjoy the same sense of calm, beauty, and connection to the water that brings us here time and again.
During your stay, we may be on the property in a separate loft apartment above the barn (when we’re not traveling). We are very mindful of your privacy and interaction preferences—we keep a low profile and are always available if and when you need us, but otherwise give you plenty of space to enjoy your stay uninterrupted.
To keep everything at its best, brief pool maintenance is completed in the early morning and typically takes just a few minutes.
Whether you're here to unwind, explore, or simply enjoy the quiet surroundings, we hope Sailor’s Retreat feels like your own private getaway.
We look forward to hosting you!
Why they chose this property
Sailor's Retreat is down a winding country road, and tucked away on a serene creek, but five minutes away are all of the things you need: a Walmart, cinemas, and restaurants. Be sure to check out Emily's produce stand. The baked goods and local produce are outstanding!
What makes this property unique
The ground level of our home is a single step up from the outside. There are two bedrooms and a full bath on the ground level. The most breathtaking aspect of the home is the view when you walk in the front door..... a six window panoramic view of the water greets you, and the water is so close, it seems to be a step beyond the patio. Every bedroom has a view of the water! As good as the water view is, the picturesque big, red, barn is a reminder that you are on rural farmland. The game room on the lower level of the barn is stocked with indoor and outdoor games and a beautiful oak bar.
Languages:
English
Premier Host
They consistently provide great experiences for their guests